ORGANIC-REACTIONS AT HIGH-PRESSURE - CONVERSION OF CYCLIC ALKANONES AND ENONES TO 1,3-DIOXOLANES
ORGANIC-REACTIONS AT HIGH-PRESSURE - CONVERSION OF CYCLIC ALKANONES AND ENONES TO 1,3-DIOXOLANES
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DOI：
10.1021/jo00375a039
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发表时间：
1986-12-12
影响因子：
3.6
通讯作者：
LOOK, GC
中科院分区：
文献类型：
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作者：
DAUBEN, WG;GERDES, JM;LOOK, GC
允许环烷酮和α，α-二取代环烷酮在15kbar(1.5 Gpa)压力下，通过在40度的苯/甲苯(7：3摩尔比)中使用乙二醇、原甲酸三乙酯和对甲苯磺酸的质子化条件进行反应。或1，2-双[(三甲基硅氧基)乙烷]与TMSOTf在20℃的二氯甲烷中的非质子化条件。质子法和非质子法均可通过加压促进反应速率的提高而导致1，3-二氧杂环戊烷8-14的生成。
Cycloalkenones and .alpha.,.alpha.-disubstituted cycloalkanones were allowed to react under 15 kbar (1.5 GPa) pressure by employing either the protic conditions of ethylene glycol, triethyl orthoformate, and p-toluenesulfonic acid in benzene/toluene (7:3 mol ratio) at 40.degree. C for 48 h or the aprotic conditions of 1,2-bis[(trimethylsilyl)oxy]ethane and TMSOTf in dichloromethane at 20.degree. C for 24 h. Both the protic and aprotic high-pressure methods brought about the formation of 1,3-dioxolanes 8-14 as a result of enhanced reaction rates promoted by the application of pressure.